EP3726991A1 - Coloured disinfectant preparation with a content of octenidine dihydrochloride - Google Patents
Coloured disinfectant preparation with a content of octenidine dihydrochlorideInfo
- Publication number
- EP3726991A1 EP3726991A1 EP18830763.1A EP18830763A EP3726991A1 EP 3726991 A1 EP3726991 A1 EP 3726991A1 EP 18830763 A EP18830763 A EP 18830763A EP 3726991 A1 EP3726991 A1 EP 3726991A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- weight
- preparation
- isopropanol
- disinfectant
- preparation according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 125
- 239000000645 desinfectant Substances 0.000 title claims abstract description 43
- SMGTYJPMKXNQFY-UHFFFAOYSA-N octenidine dihydrochloride Chemical compound Cl.Cl.C1=CC(=NCCCCCCCC)C=CN1CCCCCCCCCCN1C=CC(=NCCCCCCCC)C=C1 SMGTYJPMKXNQFY-UHFFFAOYSA-N 0.000 title claims abstract description 40
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 76
- 235000012665 annatto Nutrition 0.000 claims abstract description 57
- 244000017106 Bixa orellana Species 0.000 claims abstract description 40
- 239000010362 annatto Substances 0.000 claims abstract description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 230000000249 desinfective effect Effects 0.000 claims abstract description 8
- 238000010186 staining Methods 0.000 claims abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- 239000001670 anatto Substances 0.000 claims description 23
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 23
- ZVKOASAVGLETCT-UOGKPENDSA-N Norbixin Chemical compound OC(=O)/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C(O)=O ZVKOASAVGLETCT-UOGKPENDSA-N 0.000 claims description 20
- JERYLJRGLVHIEW-UENHKZIGSA-N Norbixin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C(=O)O)C=CC=CC=CC(=O)O JERYLJRGLVHIEW-UENHKZIGSA-N 0.000 claims description 20
- ZVKOASAVGLETCT-UOAMSCJGSA-N all-trans norbixin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C(=O)O)C=CC=C(/C)C=CC(=O)O ZVKOASAVGLETCT-UOAMSCJGSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 9
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- 238000002347 injection Methods 0.000 claims description 6
- 239000007924 injection Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000007853 buffer solution Substances 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 2
- 229940123208 Biguanide Drugs 0.000 claims description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical class OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 claims description 2
- 239000012670 alkaline solution Substances 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 150000003077 polyols Chemical class 0.000 claims description 2
- 239000000975 dye Substances 0.000 description 35
- 229960004592 isopropanol Drugs 0.000 description 24
- 229960001774 octenidine Drugs 0.000 description 17
- 239000004480 active ingredient Substances 0.000 description 11
- 230000002421 anti-septic effect Effects 0.000 description 11
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 9
- 229960003260 chlorhexidine Drugs 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- YZIYKJHYYHPJIB-UUPCJSQJSA-N chlorhexidine gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.C1=CC(Cl)=CC=C1NC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NC1=CC=C(Cl)C=C1 YZIYKJHYYHPJIB-UUPCJSQJSA-N 0.000 description 5
- 229960004756 ethanol Drugs 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 235000006010 Bixa orellana Nutrition 0.000 description 4
- 229940064004 antiseptic throat preparations Drugs 0.000 description 4
- 229960003333 chlorhexidine gluconate Drugs 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RAFGELQLHMBRHD-UHFFFAOYSA-N alpha-Fuc-(1-2)-beta-Gal-(1-3)-(beta-GlcNAc-(1-6))-GalNAc-ol Natural products COC(=O)C=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC(O)=O RAFGELQLHMBRHD-UHFFFAOYSA-N 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- RAFGELQLHMBRHD-IFNPSABLSA-N beta-Bixin Chemical compound COC(=O)\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C(O)=O RAFGELQLHMBRHD-IFNPSABLSA-N 0.000 description 3
- -1 cyclic polysaccharides Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RAFGELQLHMBRHD-VFYVRILKSA-N Bixin Natural products COC(=O)C=CC(=C/C=C/C(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C(=O)O)/C)C RAFGELQLHMBRHD-VFYVRILKSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000012978 bixa orellana Nutrition 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 229960000443 hydrochloric acid Drugs 0.000 description 2
- 235000011167 hydrochloric acid Nutrition 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 238000009593 lumbar puncture Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- RARSHUDCJQSEFJ-UHFFFAOYSA-N p-Hydroxypropiophenone Chemical compound CCC(=O)C1=CC=C(O)C=C1 RARSHUDCJQSEFJ-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 229960005335 propanol Drugs 0.000 description 2
- 238000010254 subcutaneous injection Methods 0.000 description 2
- ZVKOASAVGLETCT-LRRSNBNMSA-N (2e,4e,6e,8e,10e,12e,14e,16z,18e)-4,8,13,17-tetramethylicosa-2,4,6,8,10,12,14,16,18-nonaenedioic acid Chemical compound OC(=O)/C=C/C(/C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C(O)=O ZVKOASAVGLETCT-LRRSNBNMSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- CPKVUHPKYQGHMW-UHFFFAOYSA-N 1-ethenylpyrrolidin-2-one;molecular iodine Chemical compound II.C=CN1CCCC1=O CPKVUHPKYQGHMW-UHFFFAOYSA-N 0.000 description 1
- 229940044613 1-propanol Drugs 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- RTMBGDBBDQKNNZ-UHFFFAOYSA-L C.I. Acid Blue 3 Chemical compound [Ca+2].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=C(O)C=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1.C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=C(O)C=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 RTMBGDBBDQKNNZ-UHFFFAOYSA-L 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- UNTSJRBZLAUZBX-UHFFFAOYSA-N Isomethylbixin Natural products COC(=O)C=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC(=O)OC UNTSJRBZLAUZBX-UHFFFAOYSA-N 0.000 description 1
- 229930182559 Natural dye Natural products 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 238000002669 amniocentesis Methods 0.000 description 1
- 238000001949 anaesthesia Methods 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003260 anti-sepsis Effects 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 238000001574 biopsy Methods 0.000 description 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
- 229960002836 biphenylol Drugs 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 239000004126 brilliant black BN Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 231100000357 carcinogen Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 210000004252 chorionic villi Anatomy 0.000 description 1
- ZVKOASAVGLETCT-UHFFFAOYSA-N cis-norbixin Natural products OC(=O)C=CC(C)=CC=CC(C)=CC=CC=C(C)C=CC=C(C)C=CC(O)=O ZVKOASAVGLETCT-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000011862 kidney biopsy Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- KBPHJBAIARWVSC-RGZFRNHPSA-N lutein Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@H](O)CC1(C)C KBPHJBAIARWVSC-RGZFRNHPSA-N 0.000 description 1
- 229960005375 lutein Drugs 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000000978 natural dye Substances 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 235000012736 patent blue V Nutrition 0.000 description 1
- 239000004177 patent blue V Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000004172 quinoline yellow Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000011477 surgical intervention Methods 0.000 description 1
- 239000000979 synthetic dye Substances 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- KBPHJBAIARWVSC-XQIHNALSSA-N trans-lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C KBPHJBAIARWVSC-XQIHNALSSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- FJHBOVDFOQMZRV-XQIHNALSSA-N xanthophyll Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C=C(C)C(O)CC2(C)C FJHBOVDFOQMZRV-XQIHNALSSA-N 0.000 description 1
- 235000008210 xanthophylls Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/02—Local antiseptics
Definitions
- the present invention relates to a disinfectant preparation comprising a) octenidine dihy drochloride, b) isopropanol, c) annatto dye and d) water.
- the invention relates to a method for preparing the disinfectant preparations.
- the invention relates to said preparation for use in a method for disinfecting skin.
- the invention also relates to the use of the preparation for disinfecting skin or for staining skin.
- a colour marking of the treated surface is desirable, for example prior to a surgical intervention or during an operation.
- the active ingredients are non-ionic for example (e.g.Kodan ® Tincture forte coloured, with 45% by weight 2-propanol, 10% by weight l-propanol, 0.2% by weight 2- biphenylol, H2O2, E104, El 10 and E151).
- the group of cationic antiseptic active ingredients for skin antiseptics also includes chlor- hexidine gluconate (“chlorhexidine” below), which has been put on the US market in formula tions with 70% by volume 2-propanol (e.g. the product ChloraPrep ® from Carefusion).
- chlorhexidine chlor- hexidine gluconate
- ChloraPrep ® from Carefusion
- a potential loss of efficacy on addition of small amounts of dyes does not matter in antiseptics based on chlorhexidine.
- chlorhexidine-containing antiseptics specifically on account of the potential formation of p-chloroaniline (carcinogen, toxic) as a potential deg radation product on storage.
- chlorhexidine-containing antiseptics specifically on account of the potential formation of p-chloroaniline (carcinogen, toxic) as a potential deg radation product on storage.
- p-chloroaniline carcinogen, toxic
- W02007/130981 A2 describes aqueous solutions of chlorhexidine and a cationic dye.
- EP 2 499 913 Al is also concerned with antiseptic solutions containing chlorhexidine, and anionic dyes are proposed for the staining thereof.
- WO2016/059653 Al discloses blue-coloured chlorhexidine solutions for disinfecting skin.
- W097/46622 Al describes the use of natural or nature-identical synthetic dyes for marking or staining materials.
- the brief marking of operation areas on the skin by means of disinfectant solutions containing dye or colour pens is mentioned.
- the fact that certain active ingredients of disinfectants have a remanence effect, which must not be influenced by the dye used, is not addressed in W097/46622 Al .
- DE 40 33 690 Al discloses adducts of norbixin with water-soluble or water-dispersible proteins or branched-chain or cyclic polysaccharides.
- Norbixin is a carotenoid having two car boxylic acid groups obtained from annatto seeds.
- Bixin is the monomethyl ester of norbixin.
- the adducts are used for colouring milk for example.
- the staining of skin by coloured disin fectants is not addressed.
- the medicament and surgical skin antiseptic octeniderm ® is approved as a colourless prod uct (Schulke & Mayr GmbH, Norderstedt, Federal Republic of Germany). It contains 0.1% by weight octenidine dihydrochloride (“octenidine” for short below) as remanent active ingredient (and 30% by weight 1 -propanol, 45% by weight 2-propanol, remainder: demineralized water).
- Octenidine is a quaternary ammonium compound of the imine type (cation) with chloride as anion and its antiseptic effectiveness may be inhibited by the vast majority of anionic dyes.
- octeniderm ® contains only 0.1% octenidine, dyes added at relatively high concentration (up to 0.5%, such as in products containing chlorhexidine) for staining the skin may lead to a long-term (up to 24 h) distinct decrease in the remanent effect of octenidine.
- Non- so lid disinfectant preparations which comprise a) one or more bispyridinium alkanes and b) one or more dyes selected from xanthene dyes, azo dyes and polyterpene compounds, wherein the preparation is free of fluorescein and salts thereof.
- n-propanol is preferred over the use of isopropanol.
- An example preparation comprises 30% by weight n-propanol and 45% by weight isopropanol in addition to octenidine dihydrochloride and annatto dye.
- a disinfectant preparation comprising a) 0.02 to 0.25% by weight octenidine dihydrochloride,
- annatto dye a compound selected from the group consisting of annatto dye, wherein the amount of annatto dye is 0.005 to 0.05% by weight, specified as norbixin and based on the weight of the disinfectant preparation, and
- pH of the disinfectant preparation is 10.5 to 12.5, measured in the disinfectant preparation without components a) and b).
- the invention is based, inter alia, on preparations which have a particularly good storage stability in the defined pH range. They are outstandingly effective due to the high isopropanol content, including a remanent effect due to the octenidine content. It was surprising, further more, that the preparation according to the invention is colour-stable, although a corresponding preparation formulated with chlorhexidine is not colour-stable. It was also surprising that the disinfectant preparations according to the invention can be formulated without adding an addi tional buffer system, which is why the natural pH of the skin is not adversely altered on appli cation.
- Component a), octenidine dihydrochloride is present in preparations according to the in vention in an amount of 0.02 to 0.25% by weight, based on the weight of the preparation.
- the amount of octenidine dihydrochloride is preferably 0.03 to 0.225% by weight, more preferably 0.04 to 0.215% by weight, especially 0.05 to 0.2% by weight, such as about 0.05% by weight, or about 0.1% by weight, or about 0.2% by weight.
- the amount of octenidine dihydrochloride is particularly preferably 0.08 to 0.12% by weight, more preferably 0.09 to 0.11% by weight, based in each case on the weight of the preparation.
- the preparation according to the invention comprises at least 50% by weight isopropanol, preferably 53 to 80% by weight isopropanol, more preferably 55 to 75% by weight isopropanol, in particular 58 to 70% by weight isopropanol, more preferably 60 to 65% by weight isopropa nol, such as about 63% by weight isopropanol.
- the preparation comprises annatto dye as component c), wherein the amount of annatto dye is 0.005 to 0.05% by weight, specified as norbixin and based on the weight of the disinfectant preparation.
- the preparation preferably comprises 0.01 to 0.04% by weight annatto dye, in par ticular 0.015 to 0.025% by weight annatto dye, more preferably 0.017 to 0.022% by weight annatto dye, such as about 0.02% by weight annatto dye, specified in each case as norbixin and based on the weight of the disinfectant preparation.
- Norbixin (a xanthophyll) is a natural dye which is obtained by extracting annatto from the seeds of urucum or achiote plants (Bixa orellana).
- Norbixin may be obtained by removing the outer layer of the prepared seeds of the annatto shrub (Bixa orellana) by grinding the seeds in cold water and subsequent extraction with solvents such as acetone, methanol or hexane for example.
- the solution resulting therefrom is acidified bixin (specifically the methyl ester of the acid norbixin), which is then filtered, dried and the precipitate milled.
- the precipitate mainly comprises cis- and trans-bixin, wherein the principle dye is cis-bixin.
- Norbixin can be obtained as the corresponding salt using alkaline sodium hydroxide solution, wherein cis-norbixin is again the principle dye.
- Preparations according to the invention also contain d) water.
- Preparations according to the invention may be formulated without a mandatory buffer system and as a result do not unnecessarily influence the natural pH of (human) skin.
- Preferred preparations according to the invention do not comprise any added buffer system.
- Preferred preparations according to the invention comprise less than 35% by weight n-pro- panol, preferably less than 25% by weight n-propanol, more preferably less than 15% by weight n-propanol, especially less than 5% by weight n-propanol, wherein the preparation particularly preferably does not comprise any n-propanol.
- Preferred preparations according to the invention comprise less than 30% by weight etha nol, preferably less than 20% by weight ethanol, more preferably less than 10% by weight eth anol, especially less than 5% by weight ethanol, wherein the preparation particularly preferably does not comprise any ethanol.
- Preferred preparations according to the invention comprise less than 10% by weight aro- matic alcohol, preferably less than 5% by weight aromatic alcohol, wherein the preparation par ticularly preferably does not comprise any aromatic alcohol.
- Preferred preparations according to the invention do not comprise any glycerol, wherein the preparation preferably does not comprise any polyol.
- Preferred preparations according to the invention do not comprise any chloride, acetate or gluconate salt of l,r-hexamethylenebis[5-(4-chlorophenyl)biguanide], preferably do not com prise any biguanide or salt thereof at all.
- An example formulation of preparations according to the invention is specified below (fig- ures in % by weight):
- Preferred preparations according to the invention comprise
- octenidine dihydrochloride preferably about 0.04 to 0.215% by weight octenidine dihydrochloride
- annatto dye wherein the amount of annatto dye is 0.01 to 0.04% by weight, specified as norbixin and based on the weight of the disinfectant preparation (especially 0.015 to 0.025, such as about 0.02% by weight, specified as norbixin and based on the weight of the disinfectant preparation), and
- pH of the disinfectant preparation is about 11 to 12, measured in the disinfectant preparation without components a) and b).
- the disinfectant preparation according to the invention is a liquid aqueous-alcoholic prep- aration.
- the preparation according to the invention is preferably transparent. This facilitates the observation of disinfected areas.
- the preparation according to the invention cannot be prepared by dissolving octenidine in an aqueous phase, independently of whether the aqueous phase has already been adjusted to the desired pH or already comprises the dye. Instead, it is necessary to formulate octenidine in the aqueous-alcoholic phase. It is also not possible to formulate the annatto dye in an already for mulated aqueous-alcoholic phase. In accordance with the invention, therefore, the procedure is such that the dye is dissolved in the aqueous solution at the desired pH, in the range of 10.5 to 12.5, isopropanol is then added and finally the active ingredient octenidine is added. It is thus possible in accordance with the invention, surprisingly, to prepare the preparations specified which - optionally after filtration following addition of the octenidine active ingredient - are storage-stable even over a prolonged period.
- the invention therefore also relates to a method in which
- iii.the pH of the solution is adjusted to the desired value in the range of 10.5 to 12.5, iv. isopropanol is added and then
- the disinfectant preparations according to the invention are used on the skin in a customary manner, particularly on human skin.
- the skin on which the preparation is used is an animate skin.
- the preparation is preferably used for skin anti sepsis of undamaged skin.
- Preparations according to the invention are preferably applied to the skin in customary manner using swabs.
- the invention also relates to a disinfectant preparation for use in a method for disinfecting skin, especially in humans, wherein the preparation comprises
- octenidine dihydrochloride such as about 0.1% by weight oc- tenidine dihydrochloride
- annatto dye a compound selected from the group consisting of annatto dye, wherein the amount of annatto dye is 0.005 to 0.05% by weight, specified as norbixin and based on the weight of the disinfectant preparation, and
- the pH of the disinfectant preparation is 10.5 to 12.5, measured in the disin fectant preparation without components a) and b).
- the preparation is preferably employed for use in a method in which the method is a i) pre operative measure, ii) a measure prior to puncture or iii) a measure prior to injection.
- punctures or injections are (cf. hygiene requirements in punctures and injections - rec ommendation of the commission on hospital hygiene and prevention of infection at the Robert Koch Institute (RKI), Federal Law Gazette 2011, 54: 1135-1144, DOI 10.1007/s00103-011- 1352-8, Springer- Ver lag 2011, Tab. I therein : - s.c. injection,
- the invention also relates to the use of the preparation for disinfecting (preferably human) skin.
- the invention also relates to the use of the preparation for staining (preferably human) skin.
- staining preferably human
- the advantages of the invention are particularly apparent from the following examples. Amounts refer to weight unless otherwise stated.
- preparations 2A to 2F the procedure as in Example 1 was followed, with the difference that the active ingredient chlorhexidine gluconate was added in the final step instead of octenidine, to give preparations 2A to 2F, the composition of which is reported in Table 2.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Environmental Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102017130313.8A DE102017130313A1 (en) | 2017-12-18 | 2017-12-18 | Colored disinfecting preparation containing octenidine dihydrochloride |
PCT/EP2018/084914 WO2019121380A1 (en) | 2017-12-18 | 2018-12-14 | Coloured disinfectant preparation with a content of octenidine dihydrochloride |
Publications (2)
Publication Number | Publication Date |
---|---|
EP3726991A1 true EP3726991A1 (en) | 2020-10-28 |
EP3726991B1 EP3726991B1 (en) | 2023-12-06 |
Family
ID=65009688
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP18830763.1A Active EP3726991B1 (en) | 2017-12-18 | 2018-12-14 | Coloured disinfectant preparation with a content of octenidine dihydrochloride |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP3726991B1 (en) |
AU (1) | AU2018391507A1 (en) |
DE (1) | DE102017130313A1 (en) |
SG (1) | SG11202005248VA (en) |
WO (1) | WO2019121380A1 (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102014107412A1 (en) * | 2014-05-26 | 2015-12-17 | Schülke & Mayr GmbH | Colored disinfecting preparation based on bispyridiniumalkane |
EP3771337A1 (en) * | 2019-07-29 | 2021-02-03 | The Procter & Gamble Company | Antimicrobial composition |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5053240A (en) | 1989-10-24 | 1991-10-01 | Kalamazoo Holdings, Inc. | Norbixin adducts with water-soluble or water-dispersible proteins or branched-chain or cyclic polysaccharides |
DE19621966A1 (en) | 1996-05-31 | 1997-12-04 | Basf Ag | Use of natural or nature-identical synthetic dyes for the temporary marking or coloring of solid and liquid materials |
US20070253909A1 (en) | 2006-05-01 | 2007-11-01 | Medi-Flex, Inc. | Aqueous Antiseptic Solution and Compatible Cationic Dye for Staining Skin |
EP2499913A1 (en) | 2011-03-14 | 2012-09-19 | Combino Pharm, S.L. | Antiseptic solutions comprising chlorhexidine or its salt and an anionic dye and their preparation |
DE102014107412A1 (en) * | 2014-05-26 | 2015-12-17 | Schülke & Mayr GmbH | Colored disinfecting preparation based on bispyridiniumalkane |
US20170304467A1 (en) | 2014-10-13 | 2017-10-26 | Nex Medical Antiseptics S.R.L. | Blue dyed chlorhexidine antimicrobial composition for skin disinfection |
-
2017
- 2017-12-18 DE DE102017130313.8A patent/DE102017130313A1/en active Pending
-
2018
- 2018-12-14 AU AU2018391507A patent/AU2018391507A1/en active Pending
- 2018-12-14 SG SG11202005248VA patent/SG11202005248VA/en unknown
- 2018-12-14 WO PCT/EP2018/084914 patent/WO2019121380A1/en unknown
- 2018-12-14 EP EP18830763.1A patent/EP3726991B1/en active Active
Also Published As
Publication number | Publication date |
---|---|
AU2018391507A1 (en) | 2020-07-09 |
WO2019121380A1 (en) | 2019-06-27 |
SG11202005248VA (en) | 2020-07-29 |
DE102017130313A1 (en) | 2019-06-19 |
EP3726991B1 (en) | 2023-12-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ES2216868T3 (en) | CONCENTRATE LIQUID FOR THE CONSERVATION OF COSMETICS. | |
US20130053422A1 (en) | Antimicrobial Compositions | |
JPS62292709A (en) | Sterilizer and sterilization for skin and mucosa | |
JP4209686B2 (en) | Alcohol-free liquid concentrate for storing beauty products, household products and industrial products | |
TW201002201A (en) | Preservative blends containing quaternary ammonium compounds | |
JPH0635368B2 (en) | Composition comprising biguanide and pyrimidine having high bactericidal activity | |
EP2499913A1 (en) | Antiseptic solutions comprising chlorhexidine or its salt and an anionic dye and their preparation | |
EP2499914B1 (en) | Antiseptic solutions comprising di-(4-chlorophenyldiguanidino)-hexane and an anionic dye and their preparation | |
WO2019121380A1 (en) | Coloured disinfectant preparation with a content of octenidine dihydrochloride | |
JP4278322B2 (en) | Water-soluble chlorohexidine-containing powder, granule or tablet composition, method for producing the composition and use thereof | |
JP6833307B2 (en) | Colored bactericidal formulation based on bispiridinium alkanes | |
ES2283940T3 (en) | STABILIZING COMPOSITIONS BASED ON ETERNAL MONOALQUIL OF GLICEROL AND AROMATIC ALCOHOLS. | |
FR2791890A1 (en) | COLORED ALCOHOLIC CHLORHEXIDINE SOLUTION AND MANUFACTURING METHOD THEREOF | |
KR20200086988A (en) | Composition for Antimicrobial and Antifungal Comprising Baicalein and Wogonin as Active Ingredient | |
ES2361587T3 (en) | ANTISEPTIC SKIN COLORING. | |
EP3206492B1 (en) | Blue dyed chlorhexidine antimicrobial composition for skin disinfection | |
US9149042B2 (en) | Antiseptic solution of di(4-chloro-phenyldiguanido) compound and process therefor | |
KR20160129744A (en) | Liquid antiseptic composition and method for producing the same | |
ES2229160T3 (en) | ANTISEPTICO FOR WOUNDS AND MUCOUS MEMBRANES. | |
RU2726981C2 (en) | Skin disinfectant composition | |
CN105473139A (en) | Chlorin e6 effective for treatment, prevention or improvement of acne | |
US9907737B2 (en) | Composition comprising ferulic acid ethyl ester and aryl alkanol | |
EP4378311A1 (en) | Coloured chlorhexidine compositions | |
JP2004196712A (en) | Oil-in-water type emulsified composition | |
NO135822B (en) |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: UNKNOWN |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE |
|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE |
|
17P | Request for examination filed |
Effective date: 20200720 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
AX | Request for extension of the european patent |
Extension state: BA ME |
|
DAV | Request for validation of the european patent (deleted) | ||
DAX | Request for extension of the european patent (deleted) | ||
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: EXAMINATION IS IN PROGRESS |
|
17Q | First examination report despatched |
Effective date: 20220826 |
|
GRAP | Despatch of communication of intention to grant a patent |
Free format text: ORIGINAL CODE: EPIDOSNIGR1 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: GRANT OF PATENT IS INTENDED |
|
INTG | Intention to grant announced |
Effective date: 20230629 |
|
GRAS | Grant fee paid |
Free format text: ORIGINAL CODE: EPIDOSNIGR3 |
|
GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE PATENT HAS BEEN GRANTED |
|
AK | Designated contracting states |
Kind code of ref document: B1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
REG | Reference to a national code |
Ref country code: GB Ref legal event code: FG4D |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R096 Ref document number: 602018062324 Country of ref document: DE |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: EP |
|
REG | Reference to a national code |
Ref country code: IE Ref legal event code: FG4D |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: DE Payment date: 20231214 Year of fee payment: 6 |
|
REG | Reference to a national code |
Ref country code: LT Ref legal event code: MG9D |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: GR Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20240307 |
|
REG | Reference to a national code |
Ref country code: NL Ref legal event code: MP Effective date: 20231206 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: LT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20231206 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: ES Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20231206 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: LT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20231206 Ref country code: GR Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20240307 Ref country code: ES Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20231206 Ref country code: BG Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20240306 |
|
REG | Reference to a national code |
Ref country code: AT Ref legal event code: MK05 Ref document number: 1637507 Country of ref document: AT Kind code of ref document: T Effective date: 20231206 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: NL Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20231206 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SE Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20231206 Ref country code: RS Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20231206 Ref country code: NO Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20240306 Ref country code: NL Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20231206 Ref country code: LV Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20231206 Ref country code: HR Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20231206 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: IS Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20240406 |